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Volumn 45, Issue 45, 2006, Pages 7557-7560

Total synthesis of azumamides A and E

Author keywords

Inhibitors; Macrolactamization; Natural products; Peptides; Total synthesis

Indexed keywords

ENZYME INHIBITION; MARINE BIOLOGY; POLYPEPTIDES; STEREOCHEMISTRY;

EID: 33845202563     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602033     Document Type: Article
Times cited : (38)

References (26)
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    • For recent reviews, see: Y. Hamada, T. Shiori, Chem. Rev. 2005, 105, 4441-4482, and references therein.
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    • Hamada, Y.1    Shiori, T.2    Rev, C.3
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    • DOI: 10.1002/anie.200602047
    • Angew. Chem. Int. Ed., DOI: 10.1002/anie.200602047.
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    • (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 3186-3216
  • 8
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    • c) T. A. Miller, D. J. Witter, S. Belvedere, J. Med. Chem. 2003, 46, 5097-5116; note that the HDAC inhibition profiles observed for azumamides E and C contradict the assumption that carboxylic acids at the "zinc binding" domain give poor enzymatic activity. See Ref. [4b].
    • (2003) J. Med. Chem. , vol.46 , pp. 5097-5116
    • Miller, T.A.1    Witter, D.J.2    Belvedere, S.3
  • 10
    • 0038340749 scopus 로고    scopus 로고
    • for recent reviews, see: and references therein
    • for recent reviews, see: M. Lei, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035, and references therein.
    • (2002) Tetrahedron , vol.58 , pp. 7991-8035
    • Lei, M.1    Sibi, M.P.2
  • 11
    • 33845216327 scopus 로고    scopus 로고
    • note
    • Experimental procedures and spectroscopic data can be found in the Supporting Information.
  • 12
    • 33845196886 scopus 로고    scopus 로고
    • note
    • The acetylation was necessary for purification purposes.
  • 13
    • 33845224465 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess of compound 11 was evaluated by Mosher ester analysis of the alcohol resulting from acetate hydrolysis (see Supporting Information).
  • 16
    • 33845232403 scopus 로고    scopus 로고
    • note
    • Compound 20 was easily prepared from commercially available ethyl 4-bromobutyrate.
  • 18
    • 0033515510 scopus 로고    scopus 로고
    • M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, J. Org. Chem. 1999, 64, 2564-2566; the oxidation reaction on 24 proved to be capriciously batch-dependant. It is reported therein that the presence of carbon-carbon double bonds can be troublesome. Two-step procedures (from the alcohol to the aldehyde and from the aldehyde to the carboxylic acid) gave yields of less than 30%. Fewer problems were observed for the oxidation of 30 (Scheme 5).
    • (1999) J. Org. Chem. , vol.64 , pp. 2564-2566
    • Zhao, M.1    Li, J.2    Mano, E.3    Song, Z.4    Tschaen, D.M.5    Grabowski, E.J.J.6    Reider, P.J.7
  • 20
    • 0041475925 scopus 로고    scopus 로고
    • For recent reviews on peptide cyclizations, see: a) J. W. Davies, J. Pept. Sci. 2003, 9, 471-501;
    • (2003) J. Pept. Sci. , vol.9 , pp. 471-501
    • Davies, J.W.1
  • 24
    • 33845209771 scopus 로고    scopus 로고
    • note
    • In the macrolactamization reaction, the reagents DPPA (the successor of the conventional "azide" coupling methods) and FDPP (inducing the formation of an activated pentafluorophenyl ester) are preferred to carbodiimide-based coupling reagents, whose urea group is difficult to remove (the only exception is the water soluble carbodiimide, EDC), and to "uronium" activators (for the concurrent end-capping through tetramethylguanidylation of the amino group).
  • 25
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    • see
    • Using DPPA and BOP-Cl [bis(2-oxo-3-oxazolidinyl)phosphinic chloride (see: C. van der Auwera, M. J. O. Anteunis, Int. J. Pept. Protein Res. 1987, 29, 574-588), we observed the formation of trace amounts (ESI-MS analysis) of the cyclotetrapeptide 34 (see Supporting Information).
    • (1987) Int. J. Pept. Protein Res. , vol.29 , pp. 574-588
    • Van Der Auwera, C.1    Anteunis, M.J.O.2
  • 26
    • 33845227526 scopus 로고    scopus 로고
    • note
    • 3OD solutions (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.